5-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid → 7-(4-Acetyl-3-methyl-1-piperazinyl)-5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 373525노트

반응식

HRID 373525 반응식
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]2[CH:14]1[CH2:16][CH2:15]1.[C:21]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH:25]1[CH3:30])(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([N:24]1[CH2:29][CH2:28][N:27]([C:10]2[CH:9]=[C:8]3[C:3]([C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]3[CH:14]3[CH2:16][CH2:15]3)=[C:2]([NH2:1])[C:11]=2[F:12])[CH2:26][CH:25]1[CH3:30])(=[O:23])[CH3:22]

참가 물질

4

반응물 2

HCID 148802095-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 157294091-(2-Methylpiperazin-1-yl)ethan-1-one

생성물 1

HCID 157294107-(4-Acetyl-3-methyl-1-piperazinyl)-5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A mixture of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 1-acetyl-2-methylpiperazine and pyridine was heated under reflux for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in aqueous ammonia. The solution was neutralized with an aqueous solution of acetic acid and cooled with ice. The crystals were collected by filtration to give 7-(4-acetyl-3-methyl-1-piperazinyl)-5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. It was recrystallized from ethanol/chloroform. m.p. 269°-271° C.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in aqueous ammonia
  5. temperaturecooled with ice
  6. filtrationThe crystals were collected by filtration

출처 및 근거

ORD 기록
ord-26324228f0cc4ba489924766c6313cc9
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05164392

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